WO2021200252A1 - 有機電界発光素子 - Google Patents

有機電界発光素子 Download PDF

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WO2021200252A1
WO2021200252A1 PCT/JP2021/011289 JP2021011289W WO2021200252A1 WO 2021200252 A1 WO2021200252 A1 WO 2021200252A1 JP 2021011289 W JP2021011289 W JP 2021011289W WO 2021200252 A1 WO2021200252 A1 WO 2021200252A1
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carbon atoms
substituted
group
independently
integer
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PCT/JP2021/011289
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French (fr)
Japanese (ja)
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匡志 多田
棟智 井上
絢香 寺田
雄太 相良
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日鉄ケミカル＆マテリアル株式会社
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Application filed by 日鉄ケミカル＆マテリアル株式会社 filed Critical 日鉄ケミカル＆マテリアル株式会社
Priority to KR1020227032666A priority Critical patent/KR20220160573A/ko
Priority to EP21779365.2A priority patent/EP4130191A1/en
Priority to US17/800,786 priority patent/US20230139757A1/en
Priority to CN202180019744.6A priority patent/CN115280533A/zh
Priority to JP2022511908A priority patent/JP7690461B2/ja
Publication of WO2021200252A1 publication Critical patent/WO2021200252A1/ja
Priority to JP2025089715A priority patent/JP2025124776A/ja

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Definitions

  • the present invention relates to an organic electroluminescent device (referred to as an organic EL device).
  • the phosphorescent organic EL element that uses light emission by triplet excitons can increase the internal quantum efficiency to 100% when intersystem crossing is efficiently performed from the singlet excitons. Has been done. However, extending the life of a blue phosphorescent organic EL device has become a technical issue.
  • Patent Document 1 discloses an organic EL device using a TTF (Triplet-Triplet Fusion) mechanism, which is one of the delayed fluorescence mechanisms.
  • TTF Triplet-Triplet Fusion
  • the TTF mechanism utilizes the phenomenon that singlet excitons are generated by the collision of two triplet excitons, and it is theoretically thought that the internal quantum efficiency can be increased to 40%.
  • the efficiency is lower than that of the phosphorescent type organic EL device, further improvement in efficiency is required.
  • Patent Document 2 discloses an organic EL device using a TADF (Thermally Activated Delayed Fluorescence) mechanism.
  • the TADF mechanism utilizes the phenomenon that inverse intersystem crossing from a triplet exciter to a singlet exciter occurs in a material with a small energy difference between the singlet level and the triplet level, and theoretically determines the internal quantum efficiency. It is believed that it can be increased to 100%. However, as with the phosphorescent element, further improvement in life characteristics is required.
  • Patent Document 3 discloses an organic EL device using a TADF material represented by the following polycyclic aromatic compound as a luminescent dopant, but does not disclose practical lifetime characteristics.
  • Patent Document 4 discloses a phosphorescent organic EL element in which an indolocarbazole compound typified by the following compound and a carbazole compound are mixed in a light emitting layer and used, and is represented by the general formula (4).
  • An organic EL element having a light emitting layer mixed with a polycyclic aromatic compound and exhibiting practical life characteristics is not disclosed.
  • Patent Document 5 discloses an organic EL element in which a boron compound (a5), a TADF compound (a6), and a carbazole compound (a7) are mixed and used in a light emitting layer, but the general formula (1) or general The organic EL element showing practical life characteristics in which the first host represented by the formula (2) and the second host represented by the general formula (3) are mixed and used for the light emitting layer is not disclosed.
  • An object of the present invention is to provide a practically useful organic EL device having high efficiency and long life.
  • an organic electroluminescent element including one or more light emitting layers between an opposing anode and a cathode, at least one light emitting layer contains a host and a light emitting dopant, and the host is the general formula (1) or general.
  • the electroluminescent dopant includes a first host represented by the formula (2) and a second host represented by the general formula (3), and the luminescent dopant is a polycyclic aromatic compound represented by the general formula (4) or the general formula. It is an organic electroluminescent element characterized by containing a polycyclic aromatic compound having the structure represented by (4) as a partial structure.
  • Y 1 represents O, S, or N—Ar 1 .
  • Ar 1 independently has a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or these aromatic rings having 2 to 8 carbon atoms.
  • R 1 is independently a heavy hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, or an aromatic hydrocarbon group having 3 to 17 carbon atoms substituted or unsubstituted.
  • a independently represents an integer of 0 to 4
  • b independently represents an integer of 0 to 3.
  • c is independently an integer of 0 to 5
  • d is independently an integer of 0 to 2
  • at least one d is 1 or more.
  • e is an independently integer of 0 to 2.
  • R 2 is independently a cyano group, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted or unsubstituted 6 to 18 carbon atoms having 1 to 10 carbon atoms
  • L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms.
  • Ar 2 is a hydrogen, a cyano group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, and an aromatic hydrocarbon group having 3 to 17 carbon atoms substituted or unsubstituted. It is a heterocyclic group or a linked aromatic group formed by linking two or three of them.
  • Z 3 is an indolocarbazole ring-containing group represented by the formula (3a), and * is a bond position with L 3.
  • Ring A is a heterocycle represented by the formula (3b) and is condensed with an adjacent ring at an arbitrary position.
  • L 3 and L 31 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms or substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, respectively.
  • Ar 3 and Ar 31 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or 2 to 8 thereof. It is a linked aromatic group formed by linking pieces.
  • R 3 is an independently aliphatic hydrocarbon group having 1 to 10 carbon atoms, an substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or an substituted or unsubstituted aromatic heterocycle having 3 to 17 carbon atoms.
  • f represents an integer of 1 to 3
  • g represents an integer of 0 to 3
  • h independently represents an integer of 0 to 4
  • i represents an integer of 0 to 2
  • j represents an integer of 0 to 3. show.
  • the C ring, the D ring, and the E ring are independently an aromatic hydrocarbon ring having 6 to 24 carbon atoms or an aromatic heterocycle having 3 to 17 carbon atoms.
  • X 4 is independently O, N-Ar 4 , S, or Se.
  • R 4 and R 41 are independently aliphatic hydrocarbon groups having 1 to 10 carbon atoms, substituted or unsubstituted 6 to 18 aromatic hydrocarbon groups, or substituted or unsubstituted 3 to 17 carbon atoms.
  • Is an aromatic heterocyclic group of Ar 4 is independently composed of substituted or unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or 2 to 8 of them linked together. It is a linked aromatic group, and N-Ar 4 may be bonded to any of the C ring, D ring, or E ring to form a heterocycle containing N.
  • R 42 independently has a cyano group, a hydrocarbon, a diarylamino group having 12 to 44 carbon atoms, an aryl heteroarylamino group having 12 to 44 carbon atoms, a diheteroarylamino group having 12 to 44 carbon atoms, and a carbon number of carbon atoms.
  • v independently represents an integer of 0 to 4
  • x represents an integer of 0 to 3.
  • At least one hydrogen in the C ring, D ring, E ring, R 4 , R 41 , R 42 , and Ar 4 may be substituted with halogen or deuterium.
  • Examples of the polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure include a polycyclic aromatic compound represented by the following formula (5) or a boron-containing compound represented by the following formula (6).
  • Polycyclic aromatic compounds can be mentioned.
  • the F ring, the G ring, the H ring, the I ring, and the J ring are independently aromatic hydrocarbon rings having 6 to 24 carbon atoms or aromatic heterocycles having 3 to 17 carbon atoms. At least one hydrogen in the F ring, G ring, H ring, I ring, and J ring may be substituted with halogen or hydrocarbon.
  • X 4 , Y 4 , R 42 , x, and v agree with the general formula (4), w represents an integer of 0 to 4, y represents an integer of 0 to 3, and z represents 0 to 2. Represents an integer of.
  • X 6 independently represents N-Ar 6 , O, or S, but at least one X 6 represents N-Ar 6 .
  • Ar 6 has independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or 2 to 8 aromatic rings thereof. Representing a linked aromatic group formed by linking, N-Ar 6 may be bonded to an aromatic ring to which X 6 is bonded to form a heterocycle containing N.
  • R 6 is an independently cyano group, a hydrocarbon, a diarylamino group having 12 to 44 carbon atoms, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, Alternatively, it represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms.
  • k independently represents an integer of 0 to 4
  • l independently represents an integer of 0 to 3
  • m represents an integer of 0 to 2.
  • the first host represented by the general formula (1) is preferable, and Y 1 in the general formula (1) is preferably N—Ar 1.
  • the following formula (7) can be mentioned as a preferable general formula (1).
  • Ar 1 is synonymous with the general formula (1).
  • the light emitting layer contains a first host represented by the general formula (2) and a second host represented by the general formula (3). It is an electroluminescent element.
  • n is an integer of 1 to 5
  • p is an integer of 0 to 1
  • L 8 represents a group resulting from benzene, dibenzofuran, or dibenzothiophene.
  • R 81 represents a group derived from hydrogen, or benzene, dibenzofuran, or dibenzothiophene.
  • the difference ( ⁇ EST) between the excited singlet energy (S1) and the excited triplet energy (T1) of the luminescent dopant is preferably 0.20 eV or less, and more preferably 0.10 eV or less.
  • the light emitting layer contains 99.9 to 90 wt% of the host with respect to 0.10 to 10 wt% of the luminescent dopant, and contains 10 to 90 wt% of the first host and 90 to 10 wt% of the second host in the host. That is good.
  • an organic EL element including one or more light emitting layers between an opposing anode and a cathode, at least one light emitting layer has an excitation singlet energy (S1) and an excitation triplet energy (T1). It is an organic EL element characterized by containing an organic light emitting material having a difference ( ⁇ EST) of 0.20 eV or less, a light emitting dopant, and the first host and the second host.
  • S1 excitation singlet energy
  • T1 excitation triplet energy
  • ⁇ EST difference
  • the organic EL device of the present invention contains a specific luminescent dopant and a plurality of specific host materials in the light emitting layer, it is considered that the organic EL device can be a long-life organic EL device having a low driving voltage and high luminous efficiency. Be done.
  • the reason why the organic EL element of the present invention has a low drive voltage is that the carbazole compound, which is the first host material, has the property that holes are easily injected, and the indolocarbazole compound, which is the second host material, is injected with electrons. It is thought that it has easy characteristics, and it is assumed that holes and electrons are injected at a lower voltage to generate excitons.
  • the factor that the organic EL element of the present invention has high light emission efficiency is that the carbazole compound has a property that holes are easily injected, and the indolocarbazole compound has a property that electrons are easily injected. It is considered that the balance between holes and electrons in the light emitting layer could be maintained.
  • the reason why the organic EL element of the present invention has a long life is that when a voltage is applied to the organic EL element, holes and a second host electron composed of an indolocarbazole compound are preferentially injected into a first host composed of a carbazole compound. It is considered that this is because the electrochemical load on the luminescent dopant is reduced.
  • the organic EL device of the present invention has one or more light emitting layers between the opposing anode and cathode, and at least one light emitting layer contains a first host, a second host, and a light emitting dopant. ..
  • the first host is selected from the compounds represented by the general formula (1) or the general formula (2)
  • the second host is selected from the compounds represented by the general formula (3).
  • the luminescent dopant is selected from a polycyclic aromatic compound represented by the general formula (4) or a polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure.
  • a polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure is also referred to as a partial structure type polycyclic aromatic compound.
  • Y 1 represents O, S, or N-Ar 1 . It preferably represents O or N-Ar 1 , and more preferably N-Ar 1 .
  • a preferable mode of the general formula (1) is the general formula (7).
  • the common symbols have the same meaning.
  • Ar 1 contains independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or these aromatic rings having 2 to 8 carbon atoms.
  • Ar 1 is an unsubstituted aromatic hydrocarbon group, an aromatic heterocyclic group, or a linked aromatic group
  • Ar 1 is an unsubstituted aromatic hydrocarbon group, an aromatic heterocyclic group, or a linked aromatic group
  • benzene naphthalene, acenaphthene, acenaphthylene, azulene, anthracene, chrysene, pyrene, phenanthrene, and the like.
  • benzene, naphthalene, acenaphthene, acenaphthylene, azulene, or a group formed by taking one hydrogen from a compound composed of 2 to 4 linkages thereof can be mentioned. More preferably, groups derived from benzene, biphenyl or terphenyl can be mentioned.
  • the linked aromatic group refers to a group in which the aromatic rings of an aromatic hydrocarbon group or an aromatic heterocyclic group are linked by a single bond, and these are branched even if they are linearly linked. They may be linked and the aromatic rings may be the same or different. When it corresponds to a linked aromatic group, it is different from a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group.
  • R 1 is independently a heavy hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, or an aromatic hydrocarbon group having 3 to 17 carbon atoms substituted or unsubstituted.
  • it is an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms. be.
  • Ar 1 and R 1 are not groups derived from pyridine, pyrimidine, or triazine.
  • A represents an integer of 0 to 4
  • b represents an integer of 0 to 3.
  • a is an integer of 0 to 1
  • b is an integer of 0 to 1.
  • R 1 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms
  • R 1 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms
  • Preferred include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl.
  • R 1 is an unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms or an unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms are the same as in the above description of Ar 1 . Is.
  • the substituted aromatic hydrocarbon group or aromatic heterocyclic group or linked aromatic group may have a substituent, and examples of the substituent include a heavy hydrogen, a cyano group and a triarylsilyl group.
  • An aliphatic hydrocarbon group having 1 to 10 carbon atoms and a diarylamino group having 12 to 44 carbon atoms are preferable.
  • the substituent when the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, it may be linear, branched, or cyclic.
  • the number of substituents is 0 to 5, preferably 0 to 2.
  • the aromatic hydrocarbon group and the aromatic heterocyclic group have a substituent, the carbon number calculation does not include the carbon number of the substituent. However, it is preferable that the total number of carbon atoms including the number of carbon atoms of the substituent satisfies the above range.
  • substituents include cyano, methyl, ethyl, propyl, i-propyl, butyl, t-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, diphenylamino and naphthylphenylamino. , Dinaphthylamino, dianthranylamino, diphenanthrenylamino, dipyrenylamino and the like.
  • Preferred include cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, diphenylamino, naphthylphenylamino, or dinaphthylamino.
  • hydrogen may be deuterium. That is, in the general formulas (1) to (4) and the like, part or all of H contained in the skeleton such as carbazole and the substituents such as R 1 and Ar 1 may be deuterium.
  • c is independently an integer of 0 to 5
  • d is independently an integer of 0 to 2
  • at least one d is 1 or more
  • e is an independently integer from 0 to 2.
  • c is an integer of 1 to 2
  • the sum of the two ds is an integer of 1 to 4
  • e is an integer of 0 to 1.
  • R 2 is independently a cyano group, an aliphatic hydrocarbon group, an aromatic hydrocarbon group substituted or unsubstituted 6 to 18 carbon atoms having 1 to 10 carbon atoms. It is preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms. It is a group hydrocarbon group.
  • R 2 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms
  • R 1 is these in the general formula (1).
  • R 2 is an unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms are the same as those described in Ar 1 above.
  • L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms.
  • it is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms. More preferably, it is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms.
  • L 2 is an unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms or an unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms
  • Ar in the general formula (1) It is the same as the case where 1 is these.
  • the valence may differ.
  • L 2 is understood to be a 2d + 1 valence group.
  • Ar 2 is independently hydrogen, hydrocarbon, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, and 3 to 17 substituted or unsubstituted carbon atoms.
  • an aliphatic hydrocarbon group having 1 to 8 carbon atoms a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group.
  • Ar 2 , L 2 , and R 2 are not groups derived from pyridine, pyrimidine, or triazine.
  • Ar 2 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms
  • R 1 of the general formula (1) is these.
  • Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms is a general formula. It is the same as the case where Ar 1 of (1) is these.
  • a preferred mode of the general formula (2) is the formula (8).
  • n is an integer of 1 to 5
  • p is an integer of 0 to 1
  • n is an integer of 1 to 2
  • p is 0.
  • L 8 represents a group resulting from benzene, dibenzofuran, or dibenzothiophene.
  • R 81 represents a group derived from hydrogen, or benzene, dibenzofuran or dibenzothiophene.
  • Z 3 is an indolocarbazole ring-containing group represented by the formula (3a), and * is a bond position with L 3.
  • Ring A is a heterocycle represented by the formula (3b), and this heterocycle is condensed with an adjacent ring at an arbitrary position.
  • f represents an integer of 1 to 3, and is preferably 1.
  • g represents an integer of 0 to 3
  • j represents an integer of 0 to 3.
  • g is an integer of 0 to 2 and j is an integer of 0 to 2.
  • Preferred general formula (3) includes the following formula (9) or formula (10).
  • the formula (9) and the formula (10) the common symbols have the same meaning.
  • L 3 and L 31 independently represent substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms or substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, respectively.
  • an aromatic hydrocarbon group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 15 carbon atoms is shown. More preferably, it is a group derived from benzene, naphthalene, pyridine, triazine, dibenzofuran, or carbazole.
  • Ar 3 and Ar 31 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or 2 to 8 thereof. It is a linked aromatic group formed by linking pieces.
  • a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or 2 to 4 of these aromatic rings are linked.
  • Ar 3 and Ar 31 are preferably phenyl groups, biphenyl groups, or terphenyl groups. The terphenyl group may be linearly linked or branched. Further, benzene, carbazole, and a linked aromatic group in which 2 to 3 of these aromatic rings are linked are preferable.
  • L 3 and L 31 or Ar 3 and Ar 31 are an unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms or an aromatic heterocyclic group having 3 to 17 carbon atoms
  • benzene Naphthalene, acenaphthene, acenaftylene, azulene, anthracene, chrysene, pyrene, phenanthrene, triphenylene, fluorene, benzo [a] anthracene, tetracene, pentacene, hexacene, coronen, heptasen, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine.
  • L 3 and L 31 are groups of g + f valence or j + 1 valence.
  • Ar 3 and Ar 31 can be linked aromatic groups, but for linked aromatic groups, in the general formula (1), Ar 1 constitutes a linked aromatic group and a linked aromatic group. The same applies except that the aromatic hydrocarbon group has 6 to 30 carbon atoms. The substituents when these have a substituent are the same as the description when Ar 1 has a substituent in the general formula (1).
  • R 3 is independently an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 3 to 17 carbon atoms.
  • it is an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms. be.
  • h independently represents an integer of 0 to 4, and i represents an integer of 0 to 2.
  • h is an integer of 0 to 1 and i is an integer of 0 to 1.
  • R 3 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms is the same as in the case of R 1 , and is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group.
  • aromatic heterocyclic group having 3 to 17 carbon atoms in the above are the same as in the case where Ar 1 is these in the general formula (1).
  • the luminescent dopant used in the organic EL element of the present invention is a polycyclic aromatic compound represented by the general formula (4) or a polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure.
  • a polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure is also referred to as a partial structure type polycyclic aromatic compound.
  • the partially structured polycyclic aromatic compound is preferably a polycyclic aromatic compound represented by the formula (5), and more preferably a boron-containing polycyclic aromatic compound represented by the formula (6). It is a group compound.
  • the C ring, the D ring, the E ring, the F ring, the G ring, the H ring, the I ring and the J ring are independently aromatics having 6 to 24 carbon atoms. It is a hydrocarbon ring or an aromatic heterocycle having 3 to 17 carbon atoms, preferably an aromatic hydrocarbon ring having 6 to 20 carbon atoms or an aromatic heterocycle having 3 to 15 carbon atoms. Since the C to J rings are aromatic hydrocarbon rings or aromatic heterocycles as described above, they are also referred to as aromatic rings.
  • aromatic ring examples include benzene, naphthalene, acenaphthene, acenaphthylene, azulene, anthracene, chrysene, pyrene, phenanthrene, triphenylene, fluorene, benzo [a] anthracenepyridine, pyridine, pyrimidine, triazine, thiophene, isothiazole, Thiazol, pyridazine, pyrrol, pyrazole, imidazole, triazole, thiazazole, pyrazine, furan, isoxazole, quinoline, isoquinoline, quinoxalin, quinazoline, thiazazole, phthalazine, tetrazole, indol, benzofuran, benzothiophene, benzoxazole, benzothiazole, indazole, benz.
  • Examples thereof include a ring composed of imidazole, benzotriazole, benzoisothiazole, benzothiazyl, purine, pyranone, coumarin, isocmarin, chromone, dibenzofuran, dibenzothiophene, dibenzoselenophene, or carbazole. More preferably, it is a benzene ring, a naphthalene ring, an anthracene ring, a triphenylene ring, a phenanthrene ring, a pyrene ring, a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring.
  • P S, more preferably B.
  • R 4 and R 41 are aliphatic hydrocarbon groups having 1 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms, or substituted or unsubstituted aromatic complex having 3 to 17 carbon atoms.
  • it is an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms.
  • it is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms.
  • R 4 and R 41 are aliphatic hydrocarbon groups having 1 to 10 carbon atoms, they have substituted or unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms, or substituted or unsubstituted aromatic hydrocarbon groups having 3 to 17 carbon atoms.
  • Specific examples of the aromatic heterocyclic group are the same as in the case where R 1 in the general formula (1) is these groups.
  • X 4 is independently O, N-Ar 4 , S or Se, preferably O, N-Ar 4 or S, and more preferably O or N-Ar 4 .
  • Ar 4 is independently substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or 2 to 8 of them are linked. It is a linked aromatic group.
  • a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or 2 to 6 linkages of these aromatic rings are preferable.
  • a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 10 carbon atoms, or 2 to 4 of these aromatic rings are linked.
  • Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 8 of them are linked. Specific examples of the group group are the same as in the case where Ar 1 in the general formula (1) is these groups.
  • N-Ar 4 may be combined with an aromatic ring selected from the C ring, D ring, or E ring to form a heterocycle containing N. Further, at least one hydrogen in C ring, D ring, E ring, R 4 , R 41 , R 42 , and Ar 4 may be substituted with halogen or deuterium.
  • R 42 represents a substituent of the C ring, the D ring, and the E ring, and independently represents a cyano group, a hydrocarbon, a diarylamino group having 12 to 44 carbon atoms, and an aryl heteroarylamino group having 12 to 44 carbon atoms.
  • a diarylamino group having 12 to 36 carbon atoms Preferably, a diarylamino group having 12 to 36 carbon atoms, an aryl heteroarylamino group having 12 to 36 carbon atoms, a diheteroarylamino group having 12 to 36 carbon atoms, and an aromatic having 6 to 12 carbon atoms substituted or unsubstituted. It is a hydrocarbon group or an aromatic heterocycle having 3 to 15 carbon atoms substituted or unsubstituted. More preferably, a diarylamino group having 12 to 24 carbon atoms, an aryl heteroarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 12 to 24 carbon atoms, a substituted or unsubstituted aromatic having 6 to 10 carbon atoms. It is a group hydrocarbon group or an aromatic heterocyclic group having 3 to 12 carbon atoms substituted or unsubstituted.
  • R 42 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms are the same as in the case of R 1.
  • R 42 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms substituted or unsubstituted, or an aromatic heterocyclic group having 3 to 17 carbon atoms substituted or unsubstituted
  • Ar 1 Is similar to.
  • R 42 contains a diarylamino group having 12 to 44 carbon atoms, an aryl heteroarylamino group having 12 to 44 carbon atoms, a diheteroarylamino group having 12 to 44 carbon atoms, or an aliphatic hydrocarbon group having 1 to 10 carbon atoms.
  • Specific examples of the representations include diphenylamino, dibiphenylamino, phenylbiphenylamino, naphthylphenylamino, dinaphthylamino, dianthranylamino, diphenanthrenylamino, dipyrenylamino, dibenzofuranylphenylamino, and dibenzofuranylbiphenyl.
  • Preferred include diphenylamino, dibiphenylamino, phenylbiphenylamino, naphthylphenylamino, dinaphthylamino, dianthranylamino, diphenanthrenylamino, or dipyrenylamino. More preferably, diphenylamino, dibiphenylamino, phenylbiphenylamino, naphthylphenylamino, dinaphthylamino, dibenzofuranylphenylamino, or carbazolylphenylamino are mentioned.
  • V independently represents an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 to 1.
  • x represents an integer of 0 to 3, preferably an integer of 0 to 2, and more preferably 0 to 1.
  • a polycyclic aromatic compound having a structure represented by the general formula (4) as a partial structure will be described.
  • the polycyclic aromatic compound having the structure represented by the general formula (4) as a partial structure can be regarded as a condensate of the compound represented by the general formula (4) or a similar product thereof, and thus is a partial structure type. Also called a polycyclic aromatic compound.
  • Examples of this partially structured polycyclic aromatic compound include compounds represented by the above formula (5) or formula (6).
  • w represents an integer of 0 to 4
  • y represents an integer of 0 to 3
  • z represents an integer of 0 to 2.
  • w is 0 or 2
  • y is 0 or 1
  • z is 0 or 1.
  • the F ring to the J ring are as described above.
  • the F ring and G ring are synonymous with the C ring and D ring of the general formula (4)
  • the H ring and J ring are synonymous with the E ring
  • X 6 independently represents N-Ar 6 , O, or S, but at least one X 6 represents N-Ar 6 . It preferably represents O or N-Ar 5 , and more preferably N-Ar 5 .
  • Ar 6 agrees with Ar 4 of the general formula (4).
  • N-Ar 6 may be combined with the aromatic ring to form a heterocycle containing N.
  • Ar 3 may be directly bonded to the aromatic ring or may be bonded via a linking group.
  • R 6 is an independently cyano group, a hydrocarbon, a diarylamino group having 12 to 44 carbon atoms, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, Alternatively, it represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. Specific examples thereof are the same as in the case where R 42 is these.
  • K independently represents an integer of 0 to 4
  • l independently represents an integer of 0 to 3
  • m independently represents an integer of 0 to 2.
  • k independently represents an integer of 0 to 2
  • l represents an integer of 0 to 2
  • m is an integer of 0 to 1.
  • the partially structured polycyclic aromatic compound will be described below with reference to the formulas (5) and (6).
  • the formula (5) is composed of a structure represented by the general formula (4) and a part of the structure. From another point of view, there are two structures represented by the general formula (4), but the structure shares the I ring. That is, the structure represented by the general formula (4) is a partial structure.
  • the partially structured polycyclic aromatic compound referred to in the present invention has a structure represented by the general formula (4) as a partial structure.
  • a structure having a structure in which any of the C ring to the E ring in the general formula (4) is missing as another partial structure is suitable. Then, it is preferable that the structure represented by the general formula (4) has one as a partial structure and one to three of the other partial structures.
  • the bond between the structure represented by the general formula (4) and the other partial structure may be a bond by condensation or formation of one or more rings, or a bond by one or more bonds.
  • the partially structured polycyclic aromatic compound represented by the above formula (4-a) corresponds to, for example, a compound represented by the formula (4-64) described later. That is, the formula (4-a) is a structure in which the structure of the two general formulas (4) is shared by the central benzene ring, but includes the structural unit of the general formula (4) and has one substructure thereof. It is understood that it is a compound containing.
  • the partially structured polycyclic aromatic compound represented by the formula (4-b) corresponds to, for example, a compound represented by the formula (4-65) described later. That is, the formula (4-b) is a structure in which the structure of the two general formulas (4) is shared by the central benzene ring, but includes the structural unit of the general formula (4) and has one substructure thereof. It is understood that it is a compound containing.
  • one of X 4 is NAr 4 , which has a structure (condensed ring structure) in which a ring is formed by bonding with the other aromatic ring.
  • the partially structured polycyclic aromatic compound represented by the formula (4-c) corresponds to, for example, a compound represented by the formula (4-66) described later. That is, according to the general formula (4), the structure has a unit structure represented by the three general formulas (4) so as to share the benzene ring which is the E ring. That is, it is understood that the compound has a unit structure represented by the general formula (4) as a partial structure and contains two substructures obtained by removing one benzene ring from the general formula (4). Will be done. Further, X 4 is N-Ar 4 , which has a structure in which a ring is formed by combining with the other adjacent ring.
  • the partially structured polycyclic aromatic compounds represented by the formulas (4-d), formula (4-e), formula (4-f), and formula (4-g) are, for example, formula (4-d) described later. 67), it corresponds to the compound represented by the formula (4-68), the formula (4-69), and the formula (4-70). That is, it is a compound having two or three unit structures represented by the general formula (4) in one compound so as to share a benzene ring which is a C ring (or D ring). That is, it is understood that the compound has a unit structure represented by the general formula (4) as a partial structure and contains one partial structure which is a structure obtained by removing one benzene ring from the general formula (4). Will be done.
  • the partially structured polycyclic aromatic compounds represented by the formula (4-h) are, for example, the formulas (4-71), (4-72), (4-73) and (4-74) described later.
  • the C ring is a naphthalene ring
  • the unit structure represented by the two general formulas (4) is contained in one compound so as to share the ring.
  • It is a partially structured polycyclic aromatic compound. That is, one or two substructures having a unit structure represented by the general formula (4) as a partial structure and having one C ring (naphthalene ring) removed from the general formula (4). It is understood that it is a compound containing. Twice
  • a plurality of compounds of the general formula (4) share one or two of the rings (C ring to E ring) in the structural unit of the general formula (4). It can be said that it has a structure concatenated with each other and contains at least one structural unit of the general formula (4).
  • the number of compounds of the general formula (4) forming the above structure is 2 to 5, preferably 2 to 3.
  • the above rings (C to E rings) may be shared by one, two, or three rings.
  • polycyclic aromatic compounds represented by the general formula (4), the general formula (5) or the formula (6) and other partially structural polycyclic aromatic compounds are shown below, and these exemplary compounds are shown below. It is not limited to.
  • the organic light emitting material used as a light emitting dopant in the organic EL device of the present invention preferably has a ⁇ EST of 0.20 eV. It is more preferably 0.15 eV or less, and even more preferably 0.10 eV.
  • ⁇ EST represents the difference between the excited singlet energy (S1) and the excited triplet energy (T1).
  • S1 and T1 are according to the method described in the examples.
  • a material selected from the polycyclic aromatic compound represented by the general formula (3) or the partially structured polycyclic aromatic compound (hereinafter, also referred to as a polycyclic aromatic compound material) is used as a luminescent dopant, and the general It is excellent to use the material selected from the compound represented by the formula (1) or the general formula (2) as the first host and the material selected from the compound represented by the general formula (3) as the second host. It is possible to provide an organic EL element.
  • a compound having a ⁇ EST of 0.20 eV or less is used as the luminescent dopant together with the first host and the second host.
  • the compound as the luminescent dopant does not need to be the polycyclic aromatic compound material, as long as it is a compound having ⁇ EST of 0.20 eV or less, preferably 0.15 eV or less, and more preferably 0.10 eV. good.
  • Such compounds are known as Delayed Fluorescent Materials (TADF) in many documents, such as Patent Document 2, and can be selected from them.
  • FIG. 1 is a cross-sectional view showing a structural example of a general organic EL device used in the present invention, in which 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, and 5 is a light emitting layer. , 6 represent an electron transport layer, and 7 represents a cathode.
  • the organic EL device of the present invention may have an exciton blocking layer adjacent to the light emitting layer, or may have an electron blocking layer between the light emitting layer and the hole injection layer.
  • the exciton blocking layer can be inserted into either the anode side or the cathode side of the light emitting layer, and both can be inserted at the same time.
  • the organic EL device of the present invention has an anode, a light emitting layer, and a cathode as essential layers, but it is preferable to have a hole injection transport layer and an electron injection transport layer in addition to the essential layers, and further, a light emitting layer and electron injection. It is preferable to have a hole blocking layer between the transport layers.
  • the hole injection transport layer means either or both of the hole injection layer and the hole transport layer
  • the electron injection transport layer means either or both of the electron injection layer and the electron transport layer.
  • the structure opposite to that of FIG. 1, that is, the cathode 7, the electron transport layer 6, the light emitting layer 5, the hole transport layer 4, and the anode 2 can be laminated in this order on the substrate 1, and in this case as well, the layers can be laminated in this order. It can be added or omitted.
  • the organic EL device of the present invention is preferably supported by a substrate.
  • the substrate is not particularly limited as long as it is conventionally used for an organic EL element, and for example, a substrate made of glass, transparent plastic, quartz or the like can be used.
  • anode material in the organic EL element a material having a large work function (4 eV or more), an alloy, an electrically conductive compound, or a mixture thereof is preferably used.
  • electrode materials include metals such as Au and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2, and ZnO.
  • amorphous material such as IDIXO (In 2 O 3- ZnO) capable of producing a transparent conductive film may be used.
  • a thin film may be formed by forming a thin film of these electrode materials by a method such as thin film deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not required so much (about 100 ⁇ m or more). May form a pattern through a mask having a desired shape during vapor deposition or sputtering of the electrode material.
  • a coatable substance such as an organic conductive compound
  • a wet film forming method such as a printing method or a coating method can also be used.
  • the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, but is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • the cathode material a material having a small work function (4 eV or less) (referred to as an electron-injectable metal), an alloy, an electrically conductive compound, or a mixture thereof is used.
  • an electron-injectable metal a material having a small work function (4 eV or less)
  • an alloy an electrically conductive compound, or a mixture thereof.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O). 3 ) Examples include mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function value than this for example, magnesium / silver mixture, magnesium / Aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, lithium / aluminum mixture, aluminum and the like are suitable.
  • the cathode can be produced by forming a thin film of these cathode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission brightness is improved, which is convenient.
  • a transparent or translucent cathode can be produced. By applying this, it is possible to manufacture an element in which both the anode and the cathode are transparent.
  • the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from each of the anode and cathode, and the light emitting layer contains a light emitting dopant and a host.
  • the luminescent dopant and the host can be used so that, for example, the luminescent dopant is 0.10 to 10% and the host is 99.9 to 90%.
  • the luminescent dopant is 1.0 to 5.0% and the host is 99 to 95%, and more preferably the luminescent dopant is 1.0 to 3.0% and the host is 99 to 97%. In the present specification,% is mass% unless otherwise specified.
  • a first host represented by the general formula (1) or the general formula (2) and a second host represented by the general formula (3) are used as the host in the light emitting layer.
  • the first host and the second host can be used by, for example, 10 to 90% of the first host and 90 to 10% of the second host.
  • the first host is 30 to 70%
  • the second host is 70 to 30%
  • more preferably the first host is 40 to 60%
  • the second host is 60 to 40%.
  • one or a plurality of known hosts may be used in combination, but the amount used may be 50% or less, preferably 25% or less, based on the total amount of host materials. good.
  • the compound has a hole transporting ability and an electron transporting ability, and has a high glass transition temperature, and has T1 larger than T1 of the luminescent dopant.
  • the T1 of the host is preferably 0.010 eV or more higher than the T1 of the luminescent dopant, more preferably 0.030 eV or more, and even more preferably 0.10 eV or more.
  • a TADF-active compound may be used as the host material, and it is preferable that the difference ( ⁇ EST) between the excited singlet energy (S1) and the excited triplet energy (T1) is 0.20 eV or less.
  • the known host as the other host mentioned above is known from a large number of patent documents and the like, and can be selected from them. Specific examples of the host are not particularly limited, but are indol derivative, carbazole derivative, indolocarbazole derivative, triazole derivative, oxazole derivative, oxadiazole derivative, imidazole derivative, phenylenediamine derivative, arylamine derivative, and styryl.
  • Anthracene derivatives fluorenone derivatives, stylben derivatives, triphenylene derivatives, carborane derivatives, porphyrin derivatives, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives and metal phthalocyanine, various metal complexes represented by metal complexes of benzoxazole and benzothiazole derivatives, poly Examples thereof include polymer compounds such as (N-vinylcarbazole) derivatives, aniline-based copolymers, thiophene oligomers, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, and polyfluorene derivatives.
  • polymer compounds such as (N-vinylcarbazole) derivatives, aniline-based copolymers, thiophene oligomers, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, and polyfluorene derivatives.
  • each host can be vapor-deposited from different vapor deposition sources, or multiple types of hosts can be vapor-deposited from one vapor deposition source at the same time by premixing them before vapor deposition to form a premixture. ..
  • a method capable of mixing as uniformly as possible is desirable, and examples thereof include pulverization mixing, heating and melting under reduced pressure or in an atmosphere of an inert gas such as nitrogen, sublimation, and the like. It is not limited to the method.
  • the above polycyclic aromatic compound material or an organic light emitting material having ⁇ EST of 0.20 eV or less can be used.
  • it is the polycyclic aromatic compound material having a ⁇ EST of 0.20 eV or less.
  • the above polycyclic aromatic compound material may be used.
  • a partially structured polycyclic aromatic compound represented by the formula (5) is preferable, and a boron-containing partially structured polycyclic aromatic compound represented by the formula (6) is more preferable.
  • the ⁇ EST of the polycyclic aromatic compound material is preferably 0.20 eV or less.
  • the light emitting layer can contain two or more kinds of light emitting dopants.
  • it may be a luminescent dopant composed of the above polycyclic aromatic compound material and another compound.
  • the luminescent dopant composed of the other compounds preferably has a ⁇ EST of 0.20 eV or less, but is not limited thereto.
  • the first dopant may be the polycyclic aromatic compound material, and a known compound may be used in combination with the second dopant as another luminescent dopant. ..
  • the first dopant is preferably 0.05 to 50% with respect to the host material
  • the second dopant is preferably 0.050 to 50% with respect to the host material. The total content of the dopant and the second dopant does not exceed 50% of the host material.
  • the dopant include, but are not limited to, fused ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysen, benzoxazole derivatives and benzothiazole derivatives.
  • Benzoimidazole derivative benzotriazole derivative, oxazole derivative, oxadiazole derivative, thiazole derivative, imidazole derivative, thiadiazol derivative, triazole derivative, pyrazoline derivative, stillben derivative, thiophene derivative, tetraphenylbutadiene derivative, cyclopentadiene derivative, bisstyrylanthracene derivative And bisstyryl derivatives such as distyrylbenzene derivatives, bisstyryl arylene derivatives, diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives , Oxobenzoanthrasene derivative, xanthene derivative, rhodamine derivative, fluorescein derivative, pyryl
  • the organic light-emitting dopant and the first host or the second host are vapor-deposited from different vapor deposition sources, or premixed before vapor deposition to form a premixture, so that the light-emitting dopant and the first host can be deposited from one vapor deposition source.
  • the second host can be vapor-deposited at the same time.
  • the injection layer is a layer provided between the electrode and the organic layer in order to reduce the driving voltage and improve the emission brightness.
  • the injection layer can be provided as needed.
  • the hole blocking layer has the function of an electron transporting layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and a significantly small ability to transport holes. By blocking the above, the recombination probability of electrons and holes in the light emitting layer can be improved.
  • a known hole blocking material can be used for the hole blocking layer.
  • the material used as the second host can also be used as the material of the hole blocking layer. Further, a plurality of types of hole blocking materials may be used in combination.
  • the electron blocking layer has a function of a hole transporting layer in a broad sense, and by blocking electrons while transporting holes, the probability of recombination of electrons and holes in the light emitting layer can be improved. ..
  • As the material of the electron blocking layer a known electron blocking layer material can be used. In order to bring out the characteristics of the luminescent dopant, the material used as the first host can also be used as the material of the electron blocking layer.
  • the film thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
  • the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer, and the excitons are inserted by inserting this layer. It is possible to efficiently confine it in the light emitting layer, and it is possible to improve the light emitting efficiency of the element.
  • the exciton blocking layer can be inserted between two adjacent light emitting layers in an element in which two or more light emitting layers are adjacent to each other.
  • a known exciton blocking layer material can be used as the material of the exciton blocking layer.
  • Examples of the layer adjacent to the light emitting layer include a hole blocking layer, an electron blocking layer, an exciton blocking layer, and the like, but if these layers are not provided, the hole transport layer, the electron transport layer, and the like are the adjacent layers. Become.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer may be provided as a single layer or a plurality of layers.
  • the hole transporting material has any of hole injection, transport, and electron barrier properties, and may be either an organic substance or an inorganic substance. Any compound can be selected and used for the hole transport layer from conventionally known compounds. Examples of such hole transporting materials include porphyrin derivatives, arylamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, and styrylanthracene.
  • Derivatives fluorenone derivatives, hydrazone derivatives, stylben derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, especially thiophene oligomers, etc. may be used, but porphyrin derivatives, arylamine derivatives and styrylamine derivatives may be used. It is preferable to use an arylamine compound, and it is more preferable to use an arylamine compound.
  • the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer may be provided with a single layer or a plurality of layers.
  • the electron transporting material (which may also serve as a hole blocking material) may have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • any conventionally known compound can be selected and used.
  • a polycyclic aromatic derivative such as naphthalene, anthracene or phenanthroline, tris (8-quinolinolate) aluminum (III).
  • Derivatives phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide, freolenidene methane derivatives, anthracinodimethane and antron derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzoimidazole Derivatives, benzothiazole derivatives, indolocarbazole derivatives and the like can be mentioned. Further, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • the film forming method for each layer is not particularly limited, and it may be manufactured by either a dry process or a wet process.
  • S1 and T1 of the compounds (4-2) and (4-110) were measured.
  • S1 and T1 were measured as follows.
  • a compound (2-30) as a host and a compound (4-2) or (4-110) as a luminescent dopant are placed on a quartz substrate by a vacuum vapor deposition method under the conditions of a vacuum degree of 10 -4 Pa or less, respectively.
  • Co-deposited from different deposition sources formed a vapor deposition film with a thickness of 100 nm. At this time, co-deposited under the vapor deposition conditions where the concentration of the compound (4-2) or (4-110) was 3%.
  • S1 measures the emission spectrum of this vapor-deposited film, draws a tangent to the rising edge of the emission spectrum on the short wavelength side, and formulates the wavelength value ⁇ edge [nm] at the intersection of the tangent and the horizontal axis by the following equation ( Substitute in i) to calculate S1.
  • S1 [eV] 1239.85 / ⁇ edge (i)
  • T1 measures the phosphorescence spectrum of the above-mentioned vapor deposition film, draws a tangent line with respect to the rising edge of the phosphorescence spectrum on the short wavelength side, and sets the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis with equation (ii). Substitute in to calculate T1.
  • T1 [eV] 1239.85 / ⁇ edge (ii)
  • Example 1 Each thin film was laminated with a vacuum degree of 4.0 ⁇ 10 -5 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a film thickness of 70 nm was formed.
  • HAT-CN was formed on the ITO to a thickness of 10 nm as a hole injection layer, and then HT-1 was formed to a thickness of 25 nm as a hole transport layer.
  • compound (1-77) was formed to a thickness of 5 nm as an electron blocking layer.
  • compound (1-77) as the first host, compound (3-3) as the second host, and compound (4-110) as the luminescent dopant were co-deposited from different deposition sources to a thickness of 30 nm.
  • a light emitting layer was formed to a thickness.
  • co-deposited under the vapor deposition conditions where the concentration of the compound (4-110) was 2% and the weight ratio between the first host and the second host was 50:50.
  • a compound (HB1) was formed to a thickness of 5 nm as a hole blocking layer.
  • ET-1 was formed to a thickness of 40 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed on the electron transport layer as an electron injection layer to a thickness of 1 nm.
  • aluminum (Al) was formed as a cathode on the electron injection layer to a thickness of 70 nm to fabricate an organic EL device.
  • Examples 2 to 16 An organic EL device was produced in the same manner as in Example 1 except that the luminescent dopant, the first host, the second host, and the weight ratio of the first host to the second host were the compounds shown in Table 2.
  • Comparative Example 1 Each thin film was laminated with a vacuum degree of 4.0 ⁇ 10 -5 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a film thickness of 70 nm was formed.
  • HAT-CN was formed on the ITO to a thickness of 10 nm as a hole injection layer, and then HT-1 was formed to a thickness of 25 nm as a hole transport layer.
  • compound (2-30) was formed to a thickness of 5 nm as an electron blocking layer.
  • compound (1-77) as the first host and compound (4-110) as the luminescent dopant were co-deposited from different deposition sources to form a light emitting layer to a thickness of 30 nm.
  • a compound (HB1) was formed to a thickness of 5 nm as a hole blocking layer.
  • ET-1 was formed to a thickness of 40 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed on the electron transport layer as an electron injection layer to a thickness of 1 nm.
  • aluminum (Al) was formed as a cathode on the electron injection layer to a thickness of 70 nm to fabricate an organic EL device.
  • Comparative Examples 2, 3, 4, 7, 8, 9 An organic EL device was produced in the same manner as in Comparative Example 1 except that the luminescent dopant and the first host (without the second host) were the compounds shown in Table 2.
  • Comparative Examples 5, 6, 10 An organic EL device was produced in the same manner as in Example 1 except that the luminescent dopant, the first host, and the second host were the compounds shown in Table 2.
  • Table 3 shows the voltage of the organic EL device produced in Examples and Comparative Examples, the maximum emission wavelength of the emission spectrum, the external quantum efficiency, and the lifetime.
  • the voltage, maximum emission wavelength, and external quantum efficiency are the values when the brightness is 500 cd / m 2 , which are the initial characteristics.
  • the life was measured by measuring the time until the brightness attenuated to 50% of the initial brightness at an initial brightness of 500 cd / m 2.
  • the organic EL device of the embodiment of the present invention has characteristics of high efficiency and long life, and it can be seen that it emits blue light from the maximum emission wavelength.

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